Ammonia → 2-Nitrophenyl phenyl ether

HRID 1769828

Reaction equation

HRID 1769828 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[C:11]1([O-:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Na+].N>>[CH:14]1[CH:15]=[CH:16][C:11]([O:17][C:2]2[C:3]([N+:8]([O-:10])=[O:9])=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 69451-Chloro-2-nitrobenzeneHCID 4445035Phenolate Sodium

Product 1

HCID 166612-Nitrophenyl phenyl etherYield 93.9%

Procedure

A steel autoclave was filled with 157.6 g of o-chloronitrobenzene and 116.1 g of sodium phenolate. At room temperature, 150 g of liquid ammonia were pumped into the vessel, the mixture was heated to 600 with stirring for 15 hours and subsequently cooled. Removal of the ammonia by distillation and workup of the distillation residue gave 202 g of 2-nitrodiphenyl ether (94% of the theoretical yield), 98.5% pure.

Workup

  1. customAt room temperature
  2. temperaturethe mixture was heated to 600
  3. temperaturesubsequently cooled
  4. customRemoval of the ammonia
  5. distillationby distillation and workup of the distillation residue

Sources & evidence

ORD record
ord-26fcceed456e444982cc43b30c71f271
Source dataset
uspto-grants-1995_01
Patent number
US05382686

Linked notes

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